Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin

[Image: see text] The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki–Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a bios...

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Autores principales: Ekebergh, Andreas, Karlsson, Isabella, Mete, Rudi, Pan, Ye, Börje, Anna, Mårtensson, Jerker
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2011
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3164230/
https://www.ncbi.nlm.nih.gov/pubmed/21786790
http://dx.doi.org/10.1021/ol201812n
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author Ekebergh, Andreas
Karlsson, Isabella
Mete, Rudi
Pan, Ye
Börje, Anna
Mårtensson, Jerker
author_facet Ekebergh, Andreas
Karlsson, Isabella
Mete, Rudi
Pan, Ye
Börje, Anna
Mårtensson, Jerker
author_sort Ekebergh, Andreas
collection PubMed
description [Image: see text] The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki–Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.
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spelling pubmed-31642302011-09-01 Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin Ekebergh, Andreas Karlsson, Isabella Mete, Rudi Pan, Ye Börje, Anna Mårtensson, Jerker Org Lett [Image: see text] The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki–Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin. American Chemical Society 2011-07-25 2011-08-19 /pmc/articles/PMC3164230/ /pubmed/21786790 http://dx.doi.org/10.1021/ol201812n Text en Copyright © 2011 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Ekebergh, Andreas
Karlsson, Isabella
Mete, Rudi
Pan, Ye
Börje, Anna
Mårtensson, Jerker
Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title_full Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title_fullStr Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title_full_unstemmed Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title_short Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin
title_sort oxidative coupling as a biomimetic approach to the synthesis of scytonemin
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3164230/
https://www.ncbi.nlm.nih.gov/pubmed/21786790
http://dx.doi.org/10.1021/ol201812n
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